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Chiral separation by enantioselective liquid-liquid extraction from novel systems to continuous multistage processes

18 December 2009

Promotie: B.J.V. Verkuijl, 13.15 uur, Academiegebouw, Broerstraat 5, Groningen
Proefschrift: Chiral separation by enantioselective liquid-liquid extraction from novel systems to continuous multistage processes
Promotor(s): prof.dr. B.L. Feringa, prof.dr. J.G. de Vries, prof.dr. A.J. Minnaard
Faculteit: Wiskunde en Natuurwetenschappen
Contact: Bas Verkuijl, tel. +31647486687, basverkuijl@hotmail.com

Chiral separation by enantioselective liquid-liquid extraction from novel systems to continuous multistage processes

The principle of enantioselective liquid-liquid extraction, commonly known as ELLE, is a method for the separation of racemates.

First, the introduction of a novel extraction system for the chiral separation of benzylic primary amines is presented. As a host, phosphoric acids with a chiral BINOL backbone are used. The system is able to selectively extract primary amine enantiomers.

The experimental data are fed into a model, which in turn is applied to determine the optimal conditions for the use of a CCS cascade. A six-stage CCS cascade is used for the continuous separation of phenylglycinol, which is the first continuous chiral separation presented for a primary amine.

A novel extraction system for the chiral separation of underivatized amino acids using metal complexes with chiral ligands is introduced. The use of palladium BINAP complexes is described, which show the highest selectivity reported to date for the separation of tryptophan using metal complexes. Unprecedented high selectivities are obtained for a number of phenylalanine analogues.

The purification of a mixture of enantiopure α- and β-phenylalanine amino acids using palladium phosphine complexes is presented. The amino acid mixture was obtained by the phenylalanine aminomutase (PAM) catalyzed ammonia addition to (E) cinnamic acid.

Enantioselective liquid-liquid extraction turns out to be a valid method for the separation of racemates. This research is an important stem towards the application of ELLE in an industrial applied method for the separation of racemates.

Last modified:15 September 2017 3.38 p.m.

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